Hydrogen Bromide → Ethyl 2-bromo-1,3-thiazole-4-carboxylate

HRID 1938140Notes

Reaction equation

HRID 1938140 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](N)[S:9][CH:10]=1)=[O:5])[CH3:2].N([O-])=O.[Na+].[BrH:16]>O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:16])[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 30 g (174.3 mmol) ethyl-2-aminothiazole-4-carboxylate [prepared as in Example 1a)] in a mixture of 100 ml HBr (65%) and 100 ml of water was cooled to -15° C. and a solution of 12.03 g (174.3 mmol) sodium nitrite in 40 ml water was added over a period of 30 minutes and the mixture stirred for another 30 minutes at -15° C. After warming to room temperature, the solid was collected, washed with 50 ml cold water and dried to give 23.7 g (57.6%) ethyl-2-bromothiazole-4-carboxylate m.p. 63°-65° C.

Workup

  1. temperatureAfter warming to room temperature
  2. customthe solid was collected
  3. washwashed with 50 ml cold water
  4. customdried

Sources & evidence

ORD record
ord-a477c547d44145c68efc504b379d6707
Source dataset
uspto-grants-1997_12
Patent number
US05693594

Reaction notes

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